Chromium Mediated Organic Synthesis: The Introduction of 1,1-Dimethylallyl and Linalyl Groups on to Arenes

Neil Mathews; David A. Widdowson

doi:10.1055/s-1990-21129

Synlett 1990; 1990(8): 467-468
DOI: 10.1055/s-1990-21129

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Chromium Mediated Organic Synthesis: The Introduction of 1,1-Dimethylallyl and Linalyl Groups on to Arenes

Neil Mathews^* , David A. Widdowson

^*Department of Chemistry, Imperial College, London SW7 2AY, England

Abstract

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The synthesis of 1,1-dimethylallyl-substituted benzene-and anisoletricarbonylchromium(0) complexes was achieved in a two- or three-step sequence by the copper catalysed coupling of the lithiated arenetricarbonylchromium(0) complexes with allyl bromide followed by a double benzylic alkylation with potassium tert-butoxide/methyl iodide. For the linalyl substituted complexes the alkylations were sequential homoprenylation and methylation. Alternatively, palladium catalysed cross coupling with 2-bromo-2-butene followed by γ-deprotonation of the 1-aryl-1-propene complexes provided a more direct approach to the anionic intermediates involved.

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